Indole synthesis by controlled carbolithiation of o-aminostyrenes

A Kessler, CM Coleman, P Charoenying…

Index: Kessler, Albane; Coleman, Claire M.; Charoenying, Patchanee; O'Shea, Donal F. Journal of Organic Chemistry, 2004 , vol. 69, # 23 p. 7836 - 7846

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Citation Number: 31

Abstract

An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence ...